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Literature DB >> 10768193

Total synthesis of (+)-amphidinolide P. [corrected].

Abstract

The convergent enantiocontrolled total synthesis of the 15-membered macrolactone (-)-amphidinolide P is reported. Key transformations include a Sakurai allylation, a Stille coupling for the formation of a fully functionalized acyclic precursor, and intramolecular transesterification.

Entities: Chemical

Mesh：

Substances：

Year: 2000 PMID： 10768193 DOI： 10.1021/ol0000197

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 in total

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors: Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal: J Org Chem Date: 2004-04-02 Impact factor: 4.354

2. Antineoplastic agents. 561. Total synthesis of respirantin.

Authors: George R Pettit; Thomas H Smith; Song Feng; John C Knight; Rui Tan; Robin K Pettit; Peter A Hinrichs
Journal: J Nat Prod Date: 2007-07-04 Impact factor: 4.050

3. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors: Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal: J Org Chem Date: 2013-02-13 Impact factor: 4.354

4. Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction.

Authors: Porino Va; William R Roush
Journal: Org Lett Date: 2007-01-18 Impact factor: 6.005

Total synthesis of (+)-amphidinolide P. [corrected].

1. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

2. Antineoplastic agents. 561. Total synthesis of respirantin.

3. Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

4. Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction.

5. Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

6. Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations.

7. Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

8. Iriomoteolides-9a and 11a: two new odd-numbered macrolides from the marine dinoflagellate Amphidinium species.

9. Studies for the total synthesis of amphidinolide P.

10. Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.